NAV

Butyrfentanyl

Identification

Summary

Butyrfentanyl is a methylated fentanyl analog with no clinical indications but is commonly used as a recreational drug.

Generic Name
Butyrfentanyl
DrugBank Accession Number
DB09173
Background

Butyrfentanyl or butyrylfentanyl (not to be confused with 3-methylfentanyl) is a potent short-acting synthetic opioid analgesic drug.1 It is an analog of fentanyl with roughly 1/30 the potency.6 Butyrfentanyl was first synthesized in 1961 by Janssen Pharmaceuticals as a new opioid analgesic.6

Butyrfentanyl has no current legitimate clinical applications, but anecdotal reports indicate it may occasionally be surfacing on the grey-market as a recreational drug.6 This compound is a schedule I controlled substance in the USA because it is a positional isomer of 3-Methylfentanyl.7

The DEA in the United States has confirmed at least 40 fatalities involving butyrfentanyl before May 2016.6

Type
Small Molecule
Groups
Illicit
Structure
3D
Similar Structures
Weight
Average: 350.506
Monoisotopic: 350.235813594
Chemical Formula
C23H30N2O
Synonyms
  • Butyr-fentanyl
  • Butyrylfentanyl
External IDs
  • NIH-10486 FREE BASE
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Pharmacology

Indication

Butyrfentanyl was investigated as a potential opioid analgesic but is no longer used for this purpose.2 It is more often being used as a recreational drug.2

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Data for the pharmacodynamics of butyrfentanyl are not readily available.

Mechanism of action

Butyrfentanyl is a µ opioid receptor agonist similar to fentanyl.6

TargetActionsOrganism
AMu-type opioid receptor
agonist
Humans
UKappa-type opioid receptor
agonist
Humans
UDelta-type opioid receptor
agonist
Humans
Absorption

Data for the absorption of butyrfentanyl are not readily available.

Volume of distribution

Data for the volume of distribution of butyrfentanyl are not readily available.

Protein binding

Protein binding studies for butyrfentanyl have not been performed but due to its structural similarity with fentanyl it is likely highly bound to serum albumin and alpha-1-acid glycoprotein in circulation.5

Metabolism

Butyrfentanyl can be N-dealkylated to nor-butyrfentanyl by CYP3A4 and CYP2D6, hydroxylated to (ω-1)-hydroxy-butyrfentanyl by CYP3A4, 4'-hydroxylated to 4'-hydroxy-butyrfentanyl, hydroxylated to ω-hydroxy-butyrfentanyl bye CYP2D6 or CYP3A4, or hydroxylated to β-hydroxy-butyrfentanyl by CYP3A4.1 ω-hydroxy-butyrfentanyl is further metabolized to ω-carboxy-butyrfentanyl while 4'-hydroxy-butyrfentanyl is further metabolized to 4'-hydroxy-3'-methoxy-butyrfentanyl.1 Many of these metabolites may undergo further conjugation reactions with glucuronic acid or sulfate.1

Hover over products below to view reaction partners

Route of elimination

The route of elimination of butyrfentanyl has not been well described in the literature but most opioids are mainly eliminated in the urine.3

Half-life

Data for the half life of butyrfentanyl are not readily available.

Clearance

Data for the clearance of butyrfentanyl are not readily available.

Adverse Effects
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Toxicity

The LD50 of butyrfentanyl is not readily available.8

Patients experiencing an overdose may present with sedation, altered mental state, and difficulty breathing.4 Symptoms of overdose may be treated with naloxone and supportive measures.4

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AbataceptThe metabolism of Butyrfentanyl can be increased when combined with Abatacept.
AbirateroneThe metabolism of Butyrfentanyl can be decreased when combined with Abiraterone.
AcebutololThe metabolism of Butyrfentanyl can be decreased when combined with Acebutolol.
AcetaminophenThe metabolism of Butyrfentanyl can be decreased when combined with Acetaminophen.
AdagrasibThe metabolism of Butyrfentanyl can be decreased when combined with Adagrasib.
Food Interactions
No interactions found.

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as fentanyls. These are compounds containing the fentanyl moiety or a derivative, which is based on a N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenylpropanamide skeleton.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Fentanyls
Direct Parent
Fentanyls
Alternative Parents
Phenethylamines / Anilides / Aralkylamines / Tertiary carboxylic acid amides / Trialkylamines / Amino acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Amine / Amino acid or derivatives / Anilide / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
07V1H7R6ZN
CAS number
1169-70-6
InChI Key
QQOMYEQLWQJRKK-UHFFFAOYSA-N
InChI
InChI=1S/C23H30N2O/c1-2-9-23(26)25(21-12-7-4-8-13-21)22-15-18-24(19-16-22)17-14-20-10-5-3-6-11-20/h3-8,10-13,22H,2,9,14-19H2,1H3
IUPAC Name
N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]butanamide
SMILES
CCCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C1=CC=CC=C1

References

Synthesis Reference

Janssen PAJ. 1-Aralkyl-4-(N-aryl-carbonyl amino)piperidines and related compounds. US Patent No. US3164600 (January 5, 1965). 1965.

General References
  1. Kanamori T, Iwata YT, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Inoue H: Metabolism of Butyrylfentanyl in Fresh Human Hepatocytes: Chemical Synthesis of Authentic Metabolite Standards for Definitive Identification. Biol Pharm Bull. 2019;42(4):623-630. doi: 10.1248/bpb.b18-00765. [Article]
  2. Baumann MH, Majumdar S, Le Rouzic V, Hunkele A, Uprety R, Huang XP, Xu J, Roth BL, Pan YX, Pasternak GW: Pharmacological characterization of novel synthetic opioids (NSO) found in the recreational drug marketplace. Neuropharmacology. 2018 May 15;134(Pt A):101-107. doi: 10.1016/j.neuropharm.2017.08.016. Epub 2017 Aug 12. [Article]
  3. Smith HS: Opioid metabolism. Mayo Clin Proc. 2009 Jul;84(7):613-24. doi: 10.1016/S0025-6196(11)60750-7. [Article]
  4. Cole JB, Dunbar JF, McIntire SA, Regelmann WE, Slusher TM: Butyrfentanyl overdose resulting in diffuse alveolar hemorrhage. Pediatrics. 2015 Mar;135(3):e740-3. doi: 10.1542/peds.2014-2878. [Article]
  5. Bista SR, Haywood A, Hardy J, Lobb M, Tapuni A, Norris R: Protein binding of fentanyl and its metabolite nor-fentanyl in human plasma, albumin and alpha-1 acid glycoprotein. Xenobiotica. 2015 Mar;45(3):207-12. doi: 10.3109/00498254.2014.971093. Epub 2014 Oct 14. [Article]
  6. World Health Organization: Butyrfentanyl Critical Review Report [Link]
  7. DEA: Temporary Placement of Butyryl Fentanyl and Beta-Hydroxythiofentanyl Into Schedule I [Link]
  8. Cayman Chemicals: Butyrylfentanyl MSDS [Link]
PubChem Compound
621174
PubChem Substance
310265082
ChemSpider
539764
ZINC
ZINC000032266443
Wikipedia
Butyrfentanyl

Clinical Trials

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PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0137 mg/mLALOGPS
logP4.44ALOGPS
logP4.26Chemaxon
logS-4.4ALOGPS
pKa (Strongest Basic)8.77Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area23.55 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity108.08 m3·mol-1Chemaxon
Polarizability42.03 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ue9-1059000000-d58a827597ccc79bac6b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-3359000000-f8c9d77bb420d1d7c60b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-6b499b9224097821e94b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00mn-9046000000-e1729d9583e256cbde48
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0930000000-cc4bff1aca0aefc9489e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00b9-0920000000-cbc559b03e08e30eecaa
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-201.1263288
predicted
DarkChem Lite v0.1.0
[M-H]-183.14177
predicted
DeepCCS 1.0 (2019)
[M+H]+202.6339288
predicted
DarkChem Lite v0.1.0
[M+H]+185.53307
predicted
DeepCCS 1.0 (2019)
[M+Na]+201.4093288
predicted
DarkChem Lite v0.1.0
[M+Na]+193.56914
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Mu-type opioid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. Baumann MH, Majumdar S, Le Rouzic V, Hunkele A, Uprety R, Huang XP, Xu J, Roth BL, Pan YX, Pasternak GW: Pharmacological characterization of novel synthetic opioids (NSO) found in the recreational drug marketplace. Neuropharmacology. 2018 May 15;134(Pt A):101-107. doi: 10.1016/j.neuropharm.2017.08.016. Epub 2017 Aug 12. [Article]
  2. World Health Organization: Butyrfentanyl Critical Review Report [Link]
Details2. Kappa-type opioid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da
References
  1. Baumann MH, Majumdar S, Le Rouzic V, Hunkele A, Uprety R, Huang XP, Xu J, Roth BL, Pan YX, Pasternak GW: Pharmacological characterization of novel synthetic opioids (NSO) found in the recreational drug marketplace. Neuropharmacology. 2018 May 15;134(Pt A):101-107. doi: 10.1016/j.neuropharm.2017.08.016. Epub 2017 Aug 12. [Article]
  2. World Health Organization: Butyrfentanyl Critical Review Report [Link]
Details3. Delta-type opioid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
References
  1. Baumann MH, Majumdar S, Le Rouzic V, Hunkele A, Uprety R, Huang XP, Xu J, Roth BL, Pan YX, Pasternak GW: Pharmacological characterization of novel synthetic opioids (NSO) found in the recreational drug marketplace. Neuropharmacology. 2018 May 15;134(Pt A):101-107. doi: 10.1016/j.neuropharm.2017.08.016. Epub 2017 Aug 12. [Article]
  2. World Health Organization: Butyrfentanyl Critical Review Report [Link]

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kanamori T, Iwata YT, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Inoue H: Metabolism of Butyrylfentanyl in Fresh Human Hepatocytes: Chemical Synthesis of Authentic Metabolite Standards for Definitive Identification. Biol Pharm Bull. 2019;42(4):623-630. doi: 10.1248/bpb.b18-00765. [Article]
Details2. Cytochrome P450 2D6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Kanamori T, Iwata YT, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Inoue H: Metabolism of Butyrylfentanyl in Fresh Human Hepatocytes: Chemical Synthesis of Authentic Metabolite Standards for Definitive Identification. Biol Pharm Bull. 2019;42(4):623-630. doi: 10.1248/bpb.b18-00765. [Article]

Drug created at October 14, 2015 20:53 / Updated at June 12, 2020 16:52